A Bet to Regret
by PrisonarToYourLove
Summary: Troy Bolton and Gabriella Montez are the Golden couple of East High and are inseparable but when their two best friends quarrel they are forced apart and it's not for the best of reasons-because their friends are in an argument about which sex is the strongest and so they make a bet, a bet to see which sexist is the strongest but what about Troyella's anniversary?
1. Chapter 1

**Troyella-A Bet to Regret**

**A/N: Okay I know I have Special Ice to work on but this idea just randomly popped up in my head and it wouldn't go away so I just **_**had **_**to write it and share it with you guys because well…you guys are awesome.**

**No joke.**

**Seriously,**

**I'm not lying.**

**Stop giving me weird looks and before you even think about asking, No I am not hyper…entirely.**

**Just asking have any of you heard Remedy by Professor Green or Laser light by Jessie J because they're both AMAZING!**

**DISCLAIMER: I don't own High School Musical.**

**Don't know how long I want it maybe a very long one-shot?**

**Synopsis: Troy Bolton and Gabriella Montez are the Golden couple of East High and are inseparable but when their two best friends quarrel they are forced apart and it's not for the best of reasons because their friends are in an argument about which sex is the strongest and so they make a bet, a bet to see which sexist is the strongest but what about Troyella's anniversary? And has anyone asked Gabriella how she feels about all this? **

**Chapter 1-The Bet**

The sound of laughter can be heard throughout the hallways of East High as East High's Golden couple Troy Bolton and Gabriella Montez entered through the iron double doors and immediately all eyes were on them but they seemed completely oblivious and acted like they were the only people on the planet which caused their followers to smile.

Whenever they were insight and they were enjoying themselves it was like all the tension others were feeling was lifted off by the positive energy that they were emitting and that's why it was so magical for them because nothing and no-one could tear them apart because it was obvious that they were both utterly in love with the other and showed it everyday and night.

They have been dating ever since they were freshman, they were seniors now and there anniversary was coming soon on Sunday 30h and they couldn't wait.

They have been dating for four whole years and in about 3 days time it would be official and they were both bursting with excitement for the special occasion and no-one was more excited then Gabriella because Saturday would be the day she would prove to her parents that High School love can last.

Her parents met on a business trip so falling in high school sounded ridiculous to them but on Saturday she would prove them wrong and not even Troy knew, she was planning to make it one of her surprises because she thought her parents approval of him would be one of the best presents ever.

Troy knew she was up to something, there was this special glow about her that was radiating more then usual and he couldn't wait for what Saturday had in store for him and her seeing as he planned something but wasn't willing to tell her just yet, he'll leave that to the special day.

As they walked through the corridor they saw their friends up in the distance but something was off.

Sharpay, Kelsi and Martha were all huddled around Taylor whereas Ryan, Jason and Zeke were all huddled around Chad.

Seeing their friends apart made them look at each other questionably before the two rushed over to see what was going on and as they got nearer the more they heard.

"That's so not true." That was Taylor and you don't have to be deaf to know she's angry seeing the look on her face was good enough.

"It so is, girl's always crave for the attention they're like 'Hold me, hold me I am so scared!' You're little attention seekers!" Troy looked at his best friend in shock.

How could he say something so sexist?

He looked at his girlfriend with a worried glance, she was frozen solid.

He wasn't entirely sure about his girlfriend's beliefs but he knew she wasn't one for violence, she was always the one to calm things down and she never started fights.

"Brie?" his voice was soft and cautious but she heard it as did there friends as they turned their attention to them.

"Finally," everyone was seemingly waiting for them because of the clear exaggeration they were using.

"Hey Guys, what's going on?" Troy asked wanting to know what was going on.

"Well those girls think that we guys can't hold in our urges when it comes to_ sexual_ needs." Chad explained and Gabriella looked at her friends shocked and Troy was shocked but for a whole other reason, while Gabriella was disappointed, Troy was hurt, they were questioning his manhood.

"Well, yeah but the guys think that girls are whiny and weak and are cranky and that we can't hold in our urges." Gabriella shook her head not believing this.

"You guys are having an argument about which sex is the strongest?" Gabriella asked in disbelief.

They all nod. "Yes." As soon as they gave her an answer they continued arguing and as they were Gabriella was looking at6 Troy for help and he had that look on his face.

That look that he was thinking of something and Gabriella sighed in relief knowing he was going to do something about it but what came out of his mouth surprised even her.

"Ok if everyone wants to know which sex is the strongest then let's made a bet, a bet to see which sex can hold in their sexual urges the longest." Troy was smirking and the hold on her hand was long forgotten as his arms came up to cross in front of his chest.

Troy wasn't the only one smirking as the rest were to, with the exception of Gabriella.

"Okay then and if you _girls_ give into your urges then you have to…let me see…have to…" Chad looked deep in thought before whispering to his friends and they all had smirks on their faces.

"Well?" Sharpay asked, tapping her foot impatiently.

"You have to be our slaves for a month and do whatever we say without any complaint." The guys were full on smirking now and the girls were glaring at them; even Gabriella was giving them a slight glare.

Suddenly Sharpay smirked. "Okay and if you _guys _give into your urges," she looked at the girls and winked, "you have to let us dress you up on the next school day in the clothes we pick out, accessories included." The guys gulped.

"Alright deal."

"Okay then shall we start now?" Taylor asked and everyone nodded, minus Gabriela who was shaking her head.

She had a bad feeling about this.

What about their four-year-anniversary?

In less then an hour the whole school was informed about the bet and everyone was in to help their gender win the bet.

The guys made sure that the boys wouldn't touch the girls or even look at them and the girls did the same job as well.

Gabriella didn't really need any supervision because she was dutifully doing her work without lifting her head unless needed and everyone noticed, including Troy.

Sure Gabriella always did her work but she was never this quiet, ever.

She wasn't this quiet since freshman year and it was worrying Troy but he couldn't comfort her because he'd be losing the bet.

Why did he have to open his mouth?

Now he can't kiss his Brie.

'Great going Bolton, you really did it now.'

"Gabs you okay?" he heard Taylor ask.

"Yeah great."

Not to mention that their anniversary was this Sunday and it was Friday today.

He hoped one of the girls would give in soon, and fast.

At the corner of his eye he looked at Gabriella but her head was still down and he inwardly sighed.

The glow was gone in the blink of the eye.

The bell rang and she gathered her things and walked out without waiting for the girls.

What the hell?

It was last period and everything went just like the rest of the day, where the boys sat the very back while the girls sat at the very front and it confused the teachers to no end but continued the lesson nonetheless.

The teacher, Mr. Johnson gave the instructions out and the class continued and as usual Gabriella was being her quiet self and it was worrying everyone to no end.

The girls tried to talk to her but all they got was a few mumbles and they decided to leave her alone and try talking to her later.

She obviously wasn't in a good mood and they're sure it's probably _that _time of the month.

About halfway through the lesson a middle-aged woman with short red hair came up to Mr. Johnson and asked for Gabriella Montez.

"Yes?" Gabriella asked but Ms. Gold only smiled at her softly and handed her a yellow piece of paper that was decorated with neat cursive handwriting.

Gabriella knew that writing anywhere.

"Your parents came into the office and asked me to give this to you."

Gabriella smiled slightly. "Thank you."

Ms. Gold left but the soft smile never left her face and Troy looked at his sweetheart to see her reaction and was surprised to see the moisture come to her eyes and he wasn't the only one to notice.

Mr. Johnson came up to her. "Is everything alright Miss. Montez?"

Gabriella looked at him and Troy knew she was holding back tears.

"Yeah I'm okay, no worries."

Troy knew otherwise, he saw the way she clutched the note tightly in her delicate hand and he definitely saw the way he put the note into her pocket.

The bell rang and as soon as they were dismissed Gabriela was the first one to leave.

What was written on that note that caused Gabriella to act this way and he will find out no matter what and he knew just how to do that without his friends knowing.

It was nearing six and Gabriella had skipped making dinner for herself seeing as she didn't feel like it at this moment in time, not after what she read on that note.

She was already upset with the bet and she didn't need any more sadness but it was true.

It was official.

Her parents were staying in London for another 3 months.

They would send money for the bills, like they usually do and write but it wouldn't make a difference because they weren't here.

Most kids would love the freedom but not her, she hated it, her parents were always away, they've been gone for 4 months and the extra 2 would make it 7.

Life sucked for Gabriella Montez but she couldn't do anything about it.

Normally she would just lock herself in her room and read or do homework or even study but sometimes…Troy would come and he would wrap his arms around her and comfort her and sing to her, just for her.

Not for anyone else.

Gabriella sighed as she pulled the covers over her body.

She suddenly felt so tired and it was only six.

A knock broke her out of her tired state and she knew it wasn't from the door, it was to close and she had an idea on who it was.

Only one person used the balcony and she would normally open it straight away but they can't see each other, not now.

Not when they have a bet to complete.

Although she hated the bet she didn't want her boyfriend to be humiliated.

However, he does deserve it but she was still to nice to do such a horrible thing.

Right?

Another knock broke her out of her thoughts but she ignored it.

It could be a psycho killer for all she knew.

And another,

And another,

It stopped.

Curiosity got the best of her and she lifted the covers from her body to turn around and she saw her "boyfriend" outside with a large piece of paper about A3 with writing on it.

Gabriella hesitantly got closer and looked at what it said and her eyes softened at what it said.

'Hey, can I come in? I know I don't deserve it but I wanted to check on you, I needed to see if you're ok, and before you ask, I don't care about the bet, I was stupid.'

The Latino lifted her gaze and saw the sincerity hidden in his blue orbs and that's when she knew…he really didn't care.

Slowly unlocking the doors, never breaking eye contact she opened it and that's when he enveloped her in his arms and Gabriella never felt more at home.

They remained in silence until Gabriella broke it.

"Troy?"

"Yeah?"

"Why did you suggest the bet?"

Gabriella pulled away slightly; she wanted to see him say it.

Troy shrugged. "I don't know, I guess my ego was hurt and the competitive side in me awaked and I forgot what I was getting into, I'm sorry Brie, I was stupid."

Gabriella smiled softly and brought her petite arms to wrap around his strong torso.

"Thank you for apologizing and I forgive you."

Troy pulled away this time and gently cupped her cheek.

He gently kissed her rosy lips and both moaned in constant bliss.

It was beautiful.

When the need of air came to much they pulled apart but still had their arms wrapped around each other.

The two were cuddled lovingly together until Gabriella asked a weird question.

"So Troy you admit to be the first to give in?"

Troy nodded. "Of course, I was stupid to even agree to the bet."

Gabriella nodded satisfied. "Good."

They gently shared another peck but unknown to Troy, Gabriella had a small surprise for him tomorrow.

**So this is going to be a two-shot and I hope you can spare the time to review because I would really appreciate it.**

**Thank you.**

**PrisonarToYourLove. **


	2. Chapter 2

**Troyella-A Bet to Regret**

**Synopsis: Troy Bolton and Gabriella Montez are the Golden couple of East High and are inseparable but when their two best friends quarrel they are forced apart and it's not for the best of reasons because their friends are in an argument about which sex is the strongest and so they make a bet, a bet to see which sexist is the strongest but what about Troyella's anniversary? And has anyone asked Gabriella how she feels about all this? **

**DISCLAIMER: I don't own High School Musical**

**Chapter 2- A Surprise**

Gabriella anxiously looked at the small device in her hand and sighed.

'_This is ridiculous.' _She thought. _'Why am I so hesitant? He deserves it but it's so mean but he did start it but what if he hates me afterwards? I can't bear the thought but if he is going to break up with me then he is not worth it…even if I love him.'_

With that thought in mind Gabriella walked into the café to meet with her friends, more confident then hesitant.

When Gabriella walked in she immediately spotted her friends and walked over to them, greeting them with a small "hi".

"Okay girl what is this about?" Sharpay questioned and Gabriella sighed.

"Okay I'm not the type of person to do this but I believe Troy needs to be taught a lesson so…" Gabriella placed the small device on the middle of the table and pressed play and motioned for the girls to listen.

"_So Troy you admit to be the first to give in?"_

"_Of course, I was stupid to even agree to the bet."_

"_Good." _

The girls looked at Gabriella with huge grins.

"Perfect, so now we get to dress them up!"

Gabriella's eyes widened. "Uh…girls I just wanted to teach him a lesson I don't want to humiliate him."

The girls shook her head. "We'll see."

Just as they thought, Gabriella will always be Gabriella but they love her anyway.

However at the Bolton's house all the boys were on the edge onto breaking the bet. The separation from their girls is killing them and one thing can set off a chain reaction.

"Man we're stupid!" Chad groaned bringing his palm to slap his forehead.

All the other boys glared at him. "Don't we know it?"

"What should we do?"Zeke asked, wanting nothing more then to bring Sharpay to be in his arms.

Everyone shrugged.

Suddenly there was a knock on the door.

Troy opened the door and his eyes lit up to see his girlfriend was there but was not alone.

There behind her were her friends.

"What's going on?"

All the girls walked in leaving Troy dumbfounded.

"I'm sorry." Gabriella said to him.

"Why?" he asks.

"You'll see."

Curiosity getting the better of him Troy followed his girlfriend.

"Alright boys before you talk we have something for you to hear and Troy don't be mad at Gabi she was just mad at you." Sharpay warned as she hit the play button.

"_So Troy you admit to be the first to give in?"_

"_Of course, I was stupid to even agree to the bet."_

"_Good." _

The guys went wide-eyed.

"Unbelievable."

"Fuck."

"Shit."

"Damn."

Troy gulped. "Fuck no."

The girls, minus Gabriella smirked. "Fuck yes."

"Uh girls why don't we just leave it I mean they learnt their lesson."

Gabriella tried to reason and Taylor put an arm around her shoulder.

"Sorry Gabs but it has to be done, we'll do it and we'll leave it up to you if you want to do it to Troy or not." With that the girls dragged the guys to Sharpay's house, leaving Troyella in silence.

"Gabriella-"

"No Troy listen I admit I was mad at you for agreeing to the bet and I did want some revenge but I don't know now because I think Taylor is right with you getting what you deserve and it would be funny to see you and the other guys dressed as girls but I would never do something unless you're OK with it and-and I just need you to know that I care and love you to much!"

Troy cut her ramble off with a kiss.

"First I love you to and second thank you and lastly I'm ok with it as long as you don't show anyone that picture."

Gabriella giggled. "Well what are we waiting for, let's go!"

Troy laughed nervously.

**.**

**.**

"Gabi you came!"

Gabriella nodded. "Yep and I'm ready to turn Troy into a new person."

"Well let's start!"

The boys gulped.

"You guys ready to be feminine?"

Not a chance.

**.**

**.**

A couple of hours later the girls sat down on Sharpay's couch ready to see their finished products.

"How do you think you guys did?" Gabriella asked.

Sharpay filed her nails. "It was a piece of cake."

The girls nodded in agreement.

"Alright guys you ready to come get your picture took?" grunts could be heard from the boys as the girls got the camera app on their phone ready.

"We're coming in."

More grunts could be heard.

"5, 4, 3, 2, 1!"

Each girl entered the room their boyfriend was in and moments later they came out to share their photo.

"So?" Taylor asked and Martha giggled.

"Look at Jason." The girls did as told and laughed uncontrollably.

Sharpay patted her back. "Nicely done Martha, I am impressed."

Martha smiled. "Thanks."

There Jason was sitting on a chair with his leg popped over another with a bright orange dress that hung all the way down to his knees with matching heels that were about 2 inches high. For makeup Martha added bright pink lipstick with matching eye shadow and not to mention she added blush and his hair was put into a pigtail with an orange grip.

"I never knew orange was such a…color for Jason."

Gabriella offered Martha a high five which she gladly accepted.

"Here I'll send it to all of you." She was already texting away.

"Okay who's next?" Martha asked.

"I'll go."Kelsi offered.

"Oh I can't wait for this." Sharpay said with excitement.

Kelsi got the picture out and everyone was bursting into laughter once again.

There Ryan was leaning against a wall in a green dress that went all the way down to his feet; he had black heels that made him look somewhat taller and for makeup Kelsi applied some eye shadow, mascara, eye liner, deliberately put on to much blush and applied lip gloss on his lips while his hair was pulled into a ponytail and of course she finished it off with a pink hat.

"Brilliant!" Gabriella commented leaning into her friends shoulder.

"Thank you, I'll send it to you all."

"Alright I'll go next!" Sharpay said as she showed her friends her masterpiece.

Zeke was lying on the floor with a bright pink dress covering his corpse and on the dress was a simple pattern of a flower on the top part and the sleeves were made out of a transparent material so you could see his arms, the skirt was puffy with layers and in Zeke's hair was a single heart pin that contradicted his dark hair well, and for make up Sharpay went pink for everything and from here you could see that he was wearing silver heels in other words Zeke looked like a princess.

"Wow, who knew pink would suit him so well."

Everyone agreed as Sharpay sent everyone a copy of her masterpiece.

"Ok I'm going next." Taylor announced with a smirk.

Everyone almost fell out their seats looking at Chad, he was sitting on a chair with a red rose in his mouth as he was looking up and held one arm out and covering his body was a red dress with matching red heels and the dress had a slit on the left leg to reveal his hairy leg and the dress was strapless and Taylor added red lipstick with red nail polish and his hair was still in an afro but it held several red pins.

"Classy, I approve."

Everyone looked at Gabriella as Taylor was sending everyone a copy.

"Well I'm kind of nervous, I'm not like the rest of you guys so-"

Sharpay put a comforting hand on her shoulder. "I'm sure we'll love it."

Gabriella smiled and showed her picture and the girls gasped.

There Troy was in a blue dress that had only one strap on his left shoulder as he was looking out the window and his dress reached knee length and his hair was straightened and framed his face perfectly and you could see his blue pumps with the white bow and his hair was covered in white and blue butterfly clips, he also had some eye shadow and blush on with some nail polish. Troy looked like a schoolgirl.

"Wow you did an amazing job Gabs! I'm impressed." Sharpay praised, happy with what her friend produced.

"Do you want me to send it to you guys?" the girls looked at each other.

"Well…"Martha started.

"As much as we would love that picture," Kelsi continued.

"We all think that this picture is one of a kind," Taylor continued smiling.

"And that you should have it and anyway you're too good of a person to blackmail and I guess that's one of the reasons why Troy loves you but when the time comes use it and anyway you taught him a lesson." Sharpay finished with a huge grin.

"So should we send them back in?" Kelsi asked.

Everyone nodded.

"Let's do this."

"Boys you can come in!"

Minutes later the boys came in free of the makeup and dresses looking worried.

Sharpay rolled her eyes. "Relax we got the pictures we wanted and we won't show them to anyone under one condition."

"What condition?" Zeke asked.

"You admit girls are stronger then guys."The boys gulped but admitted it anyway.

The girls nodded satisfied. "Good."

The girls won.

**.**

**.**

The next day was Troyella's anniversary and the two were as happier as ever and Gabriella was happy that her parents finally accepted them and she was even happier that Troy has learnt his lesson and right now the two were at the park leaning against the tree.

"Beautiful." Gabriella commented.

Troy nodded. "Yeah but,"

Gabriella looked at him. "But?"

Troy looked at her. "About that picture…" Troy trailed off and Gabriella smirked.

"We'll see."

**A/N: That was it and I hope you enjoyed it, I admit it's not my best but I think it's alright. What do you think? Please leave your comments in a review.**


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